The aldol reaction has historically been one of the most important reactions for the synthesis of biologically active molecules, yet improvements in aldol reaction methods still need to be developed in order to provide shorter synthetic routes to these molecules. The objective of the proposed research is to establish a new method for catalytically forming carbon-carbon bonds using the aldol reaction. Specifically, the aim will be to couple the enolization of carbonyl compounds with their addition to aldehydes in a novel catalytic cycle. In this catalytic cycle, a labile silicon-nitrogen or silicon-oxygen bond will be cleaved to silylate a metal aldolate and simultaneously generate a base that can deprotonate a carbonyl compound. This method should overcome some of the disadvantages of other catalytic aldol reactions, which include the need to activate the carbonyl compound in a separate step and the lack of generality in these reactions. The ultimate goal of this research is to use this new catalytic reaction to induce asymmetry in the products. If successfully developed, such a method would facilitate the synthesis of complex biologically active compounds.